Umpolung of Imines Enables Catalytic Asymmetric Regio‐reversed [3+2] Cycloadditions of Iminoesters with Nitroolefins. (23rd April 2018)

• Record Type: Journal Article
• Authors: Feng, Bin; Lu, Liang‐Qiu; Chen, Jia‐Rong; Feng, Guoqiang; He, Bin‐Qing; Lu, Bin; Xiao, Wen‐Jing
• Is Part Of: Angewandte Chemie. Volume 130:Number 20(2018)
• Page Start: 5990
• Page End: 5994
• Publication Date: 2018-04-23
• Subjects: Chirale Liganden -- Cycloadditionen -- Imine -- Nitroolefine -- Umpolung; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201802492
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A copper‐catalyzed regio‐reversed asymmetric [3+2] cycloaddition of iminoesters with nitroolefins is disclosed for the first time. This method enables the facile synthesis of polysubstituted chiral pyrrolidines bearing at least one chiral quaternary center in high yields with excellent regio‐, diastereo‐, and enantioselectivity. The application of chiral P, S ligands and the unique effect of α‐aryl groups on the iminoesters are key to the success of this method. The practicality and versatility of the reaction are also demonstrated.